2-Thiopheneboronic acid → HCID 24873259, compound

HRID 2106303Notes

Reaction equation

C(OC([N:8]1[CH2:17][CH2:16][C:15]2[C:11](=[C:12](OS(C(F)(F)F)(=O)=O)[N:13]([CH2:18][CH3:19])[N:14]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[S:28]1[CH:32]=[CH:31][CH:30]=[C:29]1B(O)O>>[CH2:18]([N:13]1[C:12]([C:29]2[S:28][CH:32]=[CH:31][CH:30]=2)=[C:11]2[C:15]([CH2:16][CH2:17][NH:8][CH2:9][CH2:10]2)=[N:14]1)[CH3:19]

Participants

Reactant 2

HCID 27339602-Thiopheneboronic acid

HCID 86598381HCID 86598381, compound

Product 1

HCID 24873259HCID 24873259, compoundYield 114.1%

Procedure

The title compound (101 mg) was prepared as in Example 177, Steps C and D, using 148 mg of 2-ethyl-3-trifluoromethanesulfonyloxy-4,5,7,8-tetrahydro-2H-1,2,6-triaza-azulene-6-carboxylic acid tert-butyl ester (Example 193, Step A) and 306 mg of 2-thiopheneboronic acid. MS (ESI): exact mass calculated for C13H17N3S, 247.11; found, m/z 248.4 [M+H]+. 1H NMR (500 MHz, CDCl3): 7.62-7.57 (m, 1H), 7.16-7.11 (m, 1H), 7.10-7.05 (m, 1H), 3.98 (q, J=7.1 Hz, 2H), 3.33-3.27 (m, 2H), 3.24-3.18 (m, 2H), 3.07-3.01 (m, 2H), 2.80-2.73 (m, 2H), 1.22 (t, J=7.1 Hz, 3H).

Sources & evidence

ORD record: ord-9ebbb2241892456b8992cb245a1c9bda
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07579470B2

Reaction notes

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